281652-58-2Relevant academic research and scientific papers
An anti-diabetic drug intermediate and preparation method thereof
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Paragraph 0023-0028, (2022/01/12)
The present invention discloses an antidiabetic drug intermediate and a method for preparing it, comprising: the 2-chloro-5-iodobenzoic acid first reacted with a halogenated reagent, the reaction was complete and then added 2-fluorophene and Lewis acid fo
Facile Approach to C-Glucosides by Using a Protecting-Group-Free Hiyama Cross-Coupling Reaction: High-Yielding Dapagliflozin Synthesis
Vaňková, Karolína,Rahm, Michal,Choutka, Jan,Pohl, Radek,Parkan, Kamil
supporting information, p. 10583 - 10588 (2021/06/25)
Access to unprotected (hetero)aryl pseudo-C-glucosides via a mild Pd-catalysed Hiyama cross-coupling reaction of protecting-group-free 1-diisopropylsilyl-d-glucal with various (hetero)aryl halides has been developed. In addition, selected unprotected pseudo-C-glucosides were stereoselectively converted into the corresponding α- and β-C-glucosides, as well as 2-deoxy-β-C-glucosides. This methodology was applied to the efficient and high-yielding synthesis of dapagliflozin, a medicament used to treat type 2 diabetes mellitus. Finally, the versatility of our methodology was proved by the synthesis of other analogues of dapagliflozin.
GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS
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Page/Page column 61, (2020/06/10)
The present invention is directed to glucopyranose derivatives of formula (I), pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.
GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS
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Page/Page column 61, (2020/06/10)
The present invention is directed to glucopyranose derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.
Preparation method of empagliflozin intermediate impurity
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Paragraph 0030; 0033; 0040; 0044-0045, (2020/07/24)
The invention relates to the field of drug synthesis, in particular to a preparation method of an empagliflozin intermediate impurity (S)-3-(2-(2-chloro-5-iodobenzyl) phenoxy)tetrahydrofuran. The invention discloses a preparation method of an empagliflozi
Process development of sotagliflozin, a dual inhibitor of sodium- Glucose cotransporter-1/2 for the treatment of diabetes
Zhao, Matthew M.,Zhang, Haiming,Iimura, Shinya,Bednarz, Mark S.,Song, Qiu-Ling,Lim, Ngiap-Kie,Yan, Jie,Wu, Wenxue,Dai, Kuangchu,Gu, Xiaodong,Wang, Youchu
, p. 2689 - 2701 (2020/11/03)
The development of an efficient manufacturing process for sotagliflozin (LX4211), a dual inhibitor of sodium- glucose cotransporter-1/2 (SGLT-1/2) for the treatment of diabetes, is described. Sotagliflozin features five contiguous chiral centers on the carbohydrate core flanked by a thioether group and a biaryl moiety. Three chiral centers are obtained from the starting material L-xylose, while the other two were established (or modified) via three highly stereoselective transformations: Luche reduction (dr: 97/3), dynamic kinetic resolution of anomeric hemiacetal (dr: 95/5), and Lewis acid-promoted thiolation (dr: 1000/ 1). Global deprotection of the resulting penultimate intermediate with catalytic sodium methoxide followed by recrystallization furnishes sotagliflozin. The longest linear sequence consists of 10 steps from L-xylose with an overall yield of 40%. This process has been performed on multi-hundred kilogram batches to satisfy the drug substance development demands.
COMPOSITIONS COMPRISING (2S,3R,4R,5S,6R)-2-(4- CHLORO-3-(4-ETHOXYBENZYL)PHENYL)-6-(METHYLTHIO)TETRAHYDRO-2H-PYRAN-3,4,5-TRIOL
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Paragraph 0094, (2018/11/27)
Pharmaceutical dosage forms useful for improving the cardiovascular and/or metabolic health of patients, particularly those suffering from type 2 diabetes, are disclosed, as well as methods of their manufacture.
SGLT-2 inhibitor intermediate synthesis method
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Paragraph 0016, (2017/08/27)
The invention discloses a SGLT-2 inhibitor intermediate synthesis method. The method utilizes a NaBH4-TMSCl complex reducing agent to reduce carbonyl into methylene. The synthesis method has the characteristics of less side reactions, good environmental friendliness, low price, use of easily available raw materials and large scale production feasibility.
Preparation method of SGLT2 inhibitor intermediate
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Paragraph 0039, (2017/08/30)
The invention provides a preparation method of an SGLT2 inhibitor intermediate II. The preparation method includes that a compound V and an ethoxide reagent are subjected to nucleophilic substitution in a proper solution to obtain a compound II, wherein the compounding formula is shown as below, and X in the compound V structure is selected from Br or I. By the compounding route, the problem of purification difficulty caused by plenty of isomers in compounding routes in documentary reports is solved. Reaction operations are simple and convenient, the reagent is low in cost and easy to get, and the obtained product does not contain the isomers. The route is suitable for industrial production.
SOLID STATE FORMS OF EMPAGLIFLOZIN
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Page/Page column 41, (2017/12/29)
The present invention provides solid state forms of empagliflozin, complexes of empagliflozin with amino acids, processes for their preparation and their use in purification of empagliflozin and also provided pharmaceutical compositions comprising them and their use in therapy (Formula I).
